In North Raleigh’s Wakefield neighborhood, Winston the Bengal cat has earned a reputation as an adventurous wanderer. Known for his curious spirit, Winston regularly joined his owner, Amy Galland, on walks, explored garages, and even ventured out at night on mysterious feline errands. “He gets around,” Galland said, noting his inability to stay still. As a kitten, Winston showed a restless nature—climbing walls, tugging at his collar, and playing fetch like a terrier. He was clearly drawn to the outdoors, so Galland made the decision to let him roam, sometimes even overnight.
However, since April 4, Winston has been missing, and Galland is now reflecting on the decision that led to his disappearance. The loss has forced her to question a debate that divides many pet owners: should cats be allowed the freedom to roam, or is it better to keep them confined for their safety and well-being?
“I guess I got cocky,” Galland admitted. “I had an indoor-outdoor cat who lived to be 20. Winston could not be contained. He was desperate. I just got complacent. I’m really kicking myself.”
Despite her regret, Galland remains hopeful. Winston has a microchip, and his picture is plastered across the neighborhood, including on street signs and lampposts. He’s also listed on various lost pet websites, including Pawboost and lostmykitty.com, but so far, all reported sightings have turned out to be mistaken identity.
For some pet owners, the indoor-outdoor debate is not an issue. Take, for example, Galland’s own cat, Floyd, who prefers to stay inside as a “warm-blooded throw pillow.” But for many others, the question sparks intense discussions. Some are strongly in favor of keeping cats indoors, arguing that allowing them to roam freely is reckless and irresponsible.
One local post on the neighborhood app Nextdoor criticized pet owners who let their animals roam, calling it “willful negligence.” “A lost pet isn’t an accident,” the post read. “It’s entitlement.” Responses were mixed, with some defending the free-roaming approach: “Relax. Take a deep breath.”
Galland has felt a mix of guilt and judgment since Winston’s disappearance. She has wondered how many people are silently thinking, “This was bound to happen sooner or later.” Reflecting on her past views, she said, “I used to think the idea of locking a cat inside forever was cruel… but now, I’m forced to reconsider. I worry he’s been cat-napped, hit by a car, eaten by a coyote, or worse.”
While Raleigh does have laws in place that prohibit free-range felines, with a leash law for both cats and dogs, enforcement is often lax. In fact, Winston’s case recalls a similar situation in which Teddy, another free-roaming cat in West Raleigh, became so popular that he even launched a candidacy for mayor.
This story doesn’t present a clear-cut solution. Galland’s experience mirrors that of many pet owners who face the risks of allowing their cats outside. The author of this article has also lost indoor-outdoor cats—one to poisoning and the other to unknown circumstances. While the decision to let a cat roam is a personal one, it highlights the broader issue of how we care for our pets and the different choices we make based on their personalities.
The key takeaway is that there is no one-size-fits-all approach to raising a cat. Just as with children, every pet’s needs and behavior are unique. While it’s important to consider the risks, pet owners must also weigh the benefits of allowing their cats to explore the world around them. Ultimately, the best solution may simply be to support one another and keep an eye out for each other’s pets, whether they’re indoors or out.
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